8-FLUOROQUINOLINE Chemical Properties

Boiling point:

148 °C(Press: 30 Torr)

Density 

1.215 g/cm3(Temp: 25 °C)

refractive index 

1.60

storage temp. 

Inert atmosphere,Room Temperature

form 

clear liquid

pka

1.93±0.17(Predicted)

color 

Colorless to Light yellow to Light orange

InChI

InChI=1S/C9H6FN/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H

InChIKey

RNAAXKYOTPSFGV-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2F)C=CC=1

CAS DataBase Reference

394-68-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HS Code 

2933499090

8-FLUOROQUINOLINE Usage And Synthesis

Chemical Properties

Pale yellow solid

Synthesis

1. 85% sulfuric acid (623 g) was added to a 1 L reaction flask and o-fluoroaniline (133 g, 1.2 mol) was added slowly and dropwise. 2. The reaction mixture was heated to 130 °C and stirred at this temperature for 2 hours. 3. maintaining the reaction temperature at 130 °C, glycerol (121 g, 1.3 mol) and potassium iodide (3 g) were added slowly dropwise to the mixture. 4. After completion of the dropwise addition, the reaction mixture was continued to be stirred at 130 °C for 18 hours. 5. The reaction solution was cooled to room temperature and then slowly poured into ice water for quenching. 6. After quenching, aqueous sodium hydroxide solution was added dropwise to adjust the pH to 8-9. 7. Extraction was carried out with methyl tert-butyl ether, the oil layer was separated and concentrated. 8. The concentrate was distilled under high vacuum by means of a filled distillation column to give 8-fluoroquinoline (146 g) of high purity. 9. The yield was 83% and gas chromatographic analysis showed a purity of 99.7%.

References

[1] Patent: CN107698503, 2018, A. Location in patent: Paragraph 0061-0072
[2] Biological and Pharmaceutical Bulletin, 1997, vol. 20, # 6, p. 646 - 650

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